HUP0303436A2 - Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk - Google Patents

Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk Download PDF

Info

Publication number: HUP0303436A2
Authority: HU; Hungary
Prior art keywords: group; alkyl; compounds according; aryl; hydrogen
Prior art date: 2000-12-12

Application number

HU0303436A

Other languages

English (en)

Hungarian (hu)

Inventor

Ashok Arasappan

Kevin X. Chen

Viyyoor M. Girijavallabhan

Raymond G. Lovey

Bruce A. Malcolm

F. George Njoroge

Zhong-Yue Sun

Srikanth Venkatraman

Zhaoning Zhu

Original Assignee

Schering Corp.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-12

Filing date

2001-12-10

Publication date

2004-01-28

2001-12-10 Application filed by Schering Corp. filed Critical Schering Corp.

2004-01-28 Publication of HUP0303436A2 publication Critical patent/HUP0303436A2/hu

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 39
241000711549 Hepacivirus C Species 0.000 title description 36
108090000765 processed proteins & peptides Proteins 0.000 title description 17
102000004196 processed proteins & peptides Human genes 0.000 title description 14
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 title description 4
239000003001 serine protease inhibitor Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 213
-1 methylene- Chemical class 0.000 claims abstract description 143
125000000217 alkyl group Chemical group 0.000 claims abstract description 106
125000003342 alkenyl group Chemical group 0.000 claims abstract description 52
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 50
125000003118 aryl group Chemical group 0.000 claims abstract description 48
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 44
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 43
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 40
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 39
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
229910052717 sulfur Inorganic materials 0.000 claims abstract description 33
229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
239000001301 oxygen Substances 0.000 claims abstract description 32
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 31
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 25
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
125000000304 alkynyl group Chemical group 0.000 claims abstract description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 22
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 22
239000011593 sulfur Substances 0.000 claims abstract description 22
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 19
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 14
125000004434 sulfur atom Chemical group 0.000 claims abstract description 13
125000004429 atom Chemical group 0.000 claims abstract description 7
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 7
125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 98
239000000203 mixture Substances 0.000 claims description 79
239000001257 hydrogen Substances 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 50
150000002431 hydrogen Chemical class 0.000 claims description 38
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 33
125000003545 alkoxy group Chemical group 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 29
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
125000002877 alkyl aryl group Chemical group 0.000 claims description 28
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 23
125000000623 heterocyclic group Chemical group 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
239000004480 active ingredient Substances 0.000 claims description 22
125000003282 alkyl amino group Chemical group 0.000 claims description 22
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000001841 imino group Chemical group [H]N=* 0.000 claims description 21
125000004414 alkyl thio group Chemical group 0.000 claims description 20
125000005110 aryl thio group Chemical group 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
201000010099 disease Diseases 0.000 claims description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
125000001769 aryl amino group Chemical group 0.000 claims description 16
108091005804 Peptidases Proteins 0.000 claims description 15
239000004365 Protease Substances 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 14
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 14
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 14
125000005281 alkyl ureido group Chemical group 0.000 claims description 14
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 14
125000005421 aryl sulfonamido group Chemical group 0.000 claims description 14
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
125000004437 phosphorous atom Chemical group 0.000 claims description 14
229910052698 phosphorus Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 11
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
229910052786 argon Inorganic materials 0.000 claims description 10
125000005129 aryl carbonyl group Chemical group 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
102000014150 Interferons Human genes 0.000 claims description 8
108010050904 Interferons Proteins 0.000 claims description 8
241000700605 Viruses Species 0.000 claims description 8
125000005518 carboxamido group Chemical group 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 8
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
229940079322 interferon Drugs 0.000 claims description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 6
150000001204 N-oxides Chemical class 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 6
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 6
125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
125000003003 spiro group Chemical group 0.000 claims description 6
125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
125000003275 alpha amino acid group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
208000015181 infectious disease Diseases 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
230000000840 anti-viral effect Effects 0.000 claims description 4
125000005002 aryl methyl group Chemical group 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
229960000329 ribavirin Drugs 0.000 claims description 4
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
230000001747 exhibiting effect Effects 0.000 claims description 3
PZIDJKOIMRBQLL-UHFFFAOYSA-N $l^{2}-azanylidenemethane Chemical compound [N]=C PZIDJKOIMRBQLL-UHFFFAOYSA-N 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
150000004789 alkyl aryl sulfoxides Chemical class 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
150000005215 alkyl ethers Chemical class 0.000 claims description 2
125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
150000008378 aryl ethers Chemical class 0.000 claims description 2
125000005362 aryl sulfone group Chemical group 0.000 claims description 2
125000004421 aryl sulphonamide group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
102000006992 Interferon-alpha Human genes 0.000 claims 3
108010047761 Interferon-alpha Proteins 0.000 claims 3
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 3
239000003443 antiviral agent Substances 0.000 claims 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 1
208000005176 Hepatitis C Diseases 0.000 abstract description 10
230000008569 process Effects 0.000 abstract description 5
125000000547 substituted alkyl group Chemical group 0.000 abstract 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 abstract 1
XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 abstract 1
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 134
239000000243 solution Substances 0.000 description 108
239000000047 product Substances 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
235000019439 ethyl acetate Nutrition 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
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239000011541 reaction mixture Substances 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
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239000007787 solid Substances 0.000 description 19
239000000758 substrate Substances 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000706 filtrate Substances 0.000 description 16
235000011007 phosphoric acid Nutrition 0.000 description 16
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
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239000003112 inhibitor Substances 0.000 description 15
235000002639 sodium chloride Nutrition 0.000 description 15
101710144111 Non-structural protein 3 Proteins 0.000 description 13
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
102000035195 Peptidases Human genes 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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238000000746 purification Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
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108010022999 Serine Proteases Proteins 0.000 description 11
102000012479 Serine Proteases Human genes 0.000 description 11
229910000402 monopotassium phosphate Inorganic materials 0.000 description 11
235000019796 monopotassium phosphate Nutrition 0.000 description 11
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/81—Protease inhibitors
- C07K14/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
- C07K14/811—Serine protease (E.C. 3.4.21) inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Oncology (AREA)
Crystallography & Structural Chemistry (AREA)
Communicable Diseases (AREA)
Gastroenterology & Hepatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)

HU0303436A 2000-12-12 2001-12-10 Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk HUP0303436A2 (hu)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25486900P	2000-12-12	2000-12-12
PCT/US2001/047383 WO2002048172A2 (en)	2000-12-12	2001-12-10	Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus

Publications (1)

Publication Number	Publication Date
HUP0303436A2 true HUP0303436A2 (hu)	2004-01-28

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Application Number	Title	Priority Date	Filing Date
HU0303436A HUP0303436A2 (hu)	2000-12-12	2001-12-10	Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk

Country Status (18)

Country	Link
US (1)	US6911428B2 (de)
EP (1)	EP1343807B1 (de)
JP (1)	JP4368581B2 (de)
KR (1)	KR20030091946A (de)
CN (1)	CN1301994C (de)
AR (1)	AR031905A1 (de)
AT (1)	ATE430166T1 (de)
AU (2)	AU2002236591B2 (de)
CA (1)	CA2430458A1 (de)
DE (1)	DE60138567D1 (de)
ES (1)	ES2324594T3 (de)
HK (1)	HK1054394B (de)
HU (1)	HUP0303436A2 (de)
IL (1)	IL155842A0 (de)
MX (1)	MXPA03005219A (de)
PE (1)	PE20020691A1 (de)
WO (1)	WO2002048172A2 (de)
ZA (1)	ZA200304382B (de)

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2001
- 2001-12-10 KR KR10-2003-7007731A patent/KR20030091946A/ko not_active Withdrawn
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- 2001-12-10 MX MXPA03005219A patent/MXPA03005219A/es active IP Right Grant
- 2001-12-10 WO PCT/US2001/047383 patent/WO2002048172A2/en not_active Ceased
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- 2001-12-10 JP JP2002549703A patent/JP4368581B2/ja not_active Expired - Fee Related
- 2001-12-10 EP EP01986126A patent/EP1343807B1/de not_active Expired - Lifetime
- 2001-12-10 IL IL15584201A patent/IL155842A0/xx unknown
- 2001-12-10 US US10/013,071 patent/US6911428B2/en not_active Expired - Fee Related
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- 2001-12-10 ES ES01986126T patent/ES2324594T3/es not_active Expired - Lifetime
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- 2001-12-10 AU AU3659102A patent/AU3659102A/xx active Pending
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ES2324594T3 (es)	2009-08-11
ATE430166T1 (de)	2009-05-15
AR031905A1 (es)	2003-10-08
AU2002236591B2 (en)	2005-07-14
ZA200304382B (en)	2004-09-13
JP4368581B2 (ja)	2009-11-18
PE20020691A1 (es)	2002-08-03
EP1343807A2 (de)	2003-09-17
KR20030091946A (ko)	2003-12-03
MXPA03005219A (es)	2003-09-25
US20020147139A1 (en)	2002-10-10
AU3659102A (en)	2002-06-24
CA2430458A1 (en)	2002-06-20
IL155842A0 (en)	2003-12-23
HK1054394B (en)	2009-09-25
JP2004532812A (ja)	2004-10-28
DE60138567D1 (de)	2009-06-10
US6911428B2 (en)	2005-06-28
WO2002048172A2 (en)	2002-06-20
HK1054394A1 (en)	2003-11-28
CN1501942A (zh)	2004-06-02
WO2002048172A3 (en)	2003-06-19
EP1343807B1 (de)	2009-04-29
CN1301994C (zh)	2007-02-28

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Publication	Publication Date	Title
HUP0303436A2 (hu)	2004-01-28	Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk
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JP4298289B2 (ja)	2009-07-15	Ｃ型肝炎ウイルスのｎｓ３−セリンプロテアーゼ阻害剤としての新規ペプチド
EP2134739B1 (de)	2010-12-01	Schwefelverbindungen als hemmer der ns3-serin-protease des hepatitis-c-virus
JP4452441B2 (ja)	2010-04-21	Ｃ型肝炎ウイルスのｎｓ３−セリンプロテアーゼ阻害剤としての新規ペプチド
JP2009057390A (ja)	2009-03-19	Ｃ型肝炎ウイルスのｎｓ３セリンプロテアーゼ阻害剤としての新規ペプチド
AU2002236591A1 (en)	2002-08-29	Diaryl peptides as NS3-serine protease inhibitors of hepatits C virus
KR20060118532A (ko)	2006-11-23	Ｃ형 간염 바이러스 ｎｓ３／ｎｓ４ａ 세린 프로테아제의억제제
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